86-26-0

Hazards Identification

GHS Hazard Statements:

Not Classified
Reported as not meeting GHS hazard criteria by 1375 of 1375 companies. For more detailed information, please visit ECHA C&L website.

Usage

Uses

2-Methoxybiphenyl is used as chemical and organic intermediates.

Synthesis Reference(s)

Tetrahedron, 42, p. 2111, 1986 DOI: 10.1016/S0040-4020(01)87628-6

InChI:InChI=1/C13H12O/c1-14-13-10-6-5-9-12(13)11-7-3-2-4-8-11/h2-10H,1H3

Upstream product

• 186581-53-3 diazomethane 
• 90-43-7 2-Phenylphenol 
• 92497-07-9 6-methoxy-biphenyl-3,4'-dicarboxylic acid 
• 860589-11-3 6'-methoxy-biphenyl-2,3'-dicarboxylic acid 
• 108-86-1 bromobenzene 
• 100-66-3 methoxybenzene 
• 2684-02-8 benzenediazonium 
• 108-90-7 chlorobenzene 
• 2886-59-1 1-methoxycyclohexa-1,4-diene 
• 578-57-4 2-bromoanisole 
• 143-66-8 sodium tetraphenyl borate 
• 14774-77-7 p-methoxyphenyllithium 
• 591-51-5 phenyllithium 
• 1489-24-3 N-<(o-phenylthio)phenyl>formamide 

Downstream Products

• 725223-37-0 (5-benzyl-biphenyl-2-yl)-methyl ether 
• 258831-56-0 6-methoxy[1,1'-biphenyl]-3-carbaldehyde 
• 65-85-0 benzoic acid 
• 4556-09-6 2-phenylcyclohex-2-enone 
• 2206-48-6 2-cyclohexylanisole 
• 27124-70-5 1-(cyclohex-2-enyl)-2-methoxybenzene 
• 36702-39-3 2-Methyl-2-phenylcyclohex-3-en-1-on 
• 52316-06-0 1,4-Dihydro-2'-methoxybiphenyl 
• 142500-00-3 1-(6-methoxy-biphenyl-3-yl)-ethanone 
• 155737-90-9 η6-[(2-methoxyphenyl)benzene]tricarbonylchromium(0) 
• 155737-90-9 (C₆H₅C₆H₄OCH₃)Cr(CO)3 
• 1046158-68-2 1-(6-methoxy-biphenyl-3-yl)-12-(3-methyl-4-methoxyphenyl)dodecane-1,12-dione 
• 1308332-46-8 (6-methoxy-[1,1'-biphenyl]-3,4'-diyl)bis(phenylmethanone) 
• 856178-72-8 2-(6-methoxy-biphenyl-3-yl)-3-phenyl-quinoline-4-carboxylic acid 

Relevant academic research and scientific papers

Preparation and characterization of new palladium complex immobilized on (chitosan)/PoPD biopolymer and its catalytic application in Suzuki cross-coupling reaction

The present work reports the design, synthesis, and characterization of palladium complex immobilized on chitosan/poly(o-phenylenediamine) (CS-PoPD-Pd) for the catalytic application in the Suzuki–Miyaura C-C cross-coupling reaction through a nontoxic, inexpensive, eco-friendly, and practical method. Fourier-transform–infrared (FT-IR) spectroscopy, scanning electron microscopy (SEM), energy-dispersive X-ray spectroscopy (EDX), elemental mapping, X-ray diffraction (XRD), and inductively coupled plasma-optical emission spectrometry (ICP-OES) techniques were used for analyzing the prepared catalyst. Characterization studies showed that CS-PoPD-Pd was successfully synthesized according to our design. CS-PoPD-Pd composite demonstrated high product yield and high turnover number (TON) and turnover frequency (TOF) values with small catalyst loading for the Suzuki–Miyaura C-C cross-coupling reaction under mild reaction conditions. Besides, the synthesized CS-PoPD-Pd composite could be readily recycled and reused for at least five runs without discernible loss of its catalytic activity.

'Awaken' aryl sulfonyl fluoride: a new partner in the Suzuki-Miyaura coupling reaction

An example of the activation of the -SO2F group, which is traditionally considered a stable group even in the presence of a transition metal, is described using a novel partner in the Suzuki-Miyaura coupling reaction catalyzed by Pd(OAc)2 and Ruphos as ligands. The products showed good to outstanding yields and broad functional group compatibility under optimal conditions. The sequential synthesis of non-symmetric terphenyls and the gram grade process highlight the approach's synthetic utility. DFT calculations have shown that Pd0 prefers to insert between C-S bonds rather than S-F bonds. This journal is

Nickel-Catalyzed Direct Cross-Coupling of Aryl Sulfonium Salt with Aryl Bromide

The direct cross-couplings of aryl sulfonium salts with aryl halides could be achieved by using nickel as a reaction catalyst. The reactions proceeded efficiently via C-S bond activation in the presence of magnesium turnings and lithium chloride in THF at ambient temperature to afford the corresponding biaryls in moderate to good yields, potentially serving as an attractive alternative to conventional cross-coupling reactions employing preprepared organometallic reagents.

Aromatization as the driving force for single electron transfer towards C-C cross-coupling reactions

There is a strong current interest in C-H functionalization reactions under metal-free conditions. We report herein the deprotonated form of dihydrophenazine (DPh) as a potent initiator under photochemical conditions that can efficiently generate aryl radicals via single electron transfer (SET). The driving force for such electron transfer is the gain in aromaticity for the initiator molecule. Using this methodology, a series of arenes and heteroarenes have been cross-coupled with aryls at room temperature. Photochemical activation of DPh anions and the subsequent electron transfer to substrate aryldiazonium salts have been proved by Stern-Volmer kinetic analysis. Detailed mechanistic studies including interception of important reaction intermediates prove the aromaticity-driven SET as the key step to generate aryl radicals towards radical-promoted cross-coupling reactions.

Triptycene ring metal palladium compound and application thereof

The invention discloses a triptycene cyclometalated palladium compound and an application thereof. The triptycene cyclometalated palladium compound has the following general formula, wherein three RAscan be the same or different and are respectively and independently expressed as R1-(Z1-A1-Z2)x-,wherein the three RBs can be the same or different and are respectively and independently expressed asR2-(Z3-A2-Z4)y-, the two RCs may be the same or different, each independently expressed as R3-(Z5-A3-Z6)z-. The triptycene cyclometalated palladium compound provided by the invention has a triptycenelarge-steric-hindrance group, and can stabilize a zero-valent palladium intermediate in a catalytic cycle, so that the catalytic efficiency is improved, the use amount of a catalyst can be reduced tobe less than ten thousandth, and the compound is simple in synthesis step, high in yield, relatively low in cost and suitable for various substrates, and the method has an important application valuefor researching the progress and application of the coupling reaction.

Pd-NHCs Enabled Suzuki-Miyaura Cross-Coupling of Arylhydrazines via C–N Bond Cleavage

We describe a highly efficient protocol for cross-coupling of phenylhydrazines with arylboronic acids by Pd-NHCs under aerobic reaction condition. A series of well-defined Pd-NHCs complexes were evaluated and the relationship between the structure and the catalytic properties was investigated. It was disclosed that the Pd-PEPPSI-IPr proved to be the robust precatalyst, providing access to a range of (hetero)biaryls in good to excellent yields.

Preparation of Ni-microsphere and Cu-MOF using aspartic acid as coordinating ligand and study of their catalytic properties in Stille and sulfoxidation reactions

In this study, the thermal and catalytic behavior of Ni-microsphere and Cu-MOF were investigated with aspartic acid as the coordinating ligand with different morphologies. The Ni-microsphere and Cu-MOF with aspartic acid, as the coordinating ligand, were prepared via a solvothermal method. The morphology and porosity of the obtained Ni microsphere and Cu-MOF were characterized by XRD, FTIR, TGA, DSC, BET and SEM techniques. The catalytic activity of the Ni-microsphere and Cu-MOF was examined in Stille and sulfoxidation reactions. The Ni microsphere and Cu-MOF were easily isolated from the reaction mixtures by simple filtration and then recycled four times without any reduction of catalytic efficiency.

Porous Organic Phenanthroline-Based Polymer as an Efficient Transition-Metal-Free Heterogeneous Catalyst for Direct Aromatic C?H Activation

Direct C?H bond transformation has been regarded as one of the most important areas in organic synthesis in both academia and industry. However, the heterogeneous transition-metal-free catalysis of direct C?H bond transformation has remained a contemporary challenge. To tackle this challenge, we designed and constructed a porous phenanthroline-based polymer (namely POP-Phen) via free radical polymerization of vinyl-functionalized phenanthroline monomers. POP-Phen shows excellent catalytic performances in transition-metal-free catalyzed C?H arylation, even better than those of the corresponding homogeneous catalyst, which is mainly attributed to the high density of catalytically active sites in the heterogeneous catalyst. Kinetic isotope experiments and spectral characterizations demonstrate the electron-transfer between the heterogeneous catalyst and the base (t-BuOK), a key step for C?H activation. We believe that this porous organic phenanthroline polymer could open a new door for the design of novel heterogeneous transition-metal-free catalysts for direct C?H activation.

Nickel(II) complexes with N,O-donor thiopseudourea ligands: Syntheses, structures, and catalytic applications in Kumada–Corriu cross-coupling reactions

Synthesis, characterization, and physical properties of benzyl-N′-(4-R-benzoyl)-N-(2,6-diisopropylphenyl)carbamimidothioates, HL1 (R = H) and HL2 (R = Cl), and their nickel(II) complexes having the general molecular formula [Ni(L1/2)2] (1 and 2) have been reported. Elemental analysis, magnetic susceptibility, solution electrical conductivity, and various spectroscopic (IR, UV–Vis, and 1H NMR) measurements were used to characterize HL1, HL2, and the two complexes (1 and 2). The molecular structures of all four compounds were determined by single-crystal X-ray crystallographic studies. The structures of HL1 and HL2 showed the imino-ketone form of both compounds. In each of 1 and 2, the six-membered chelate ring forming iminolate-O and azomethine-N donor two (L1/2)? ligands form a square-planar trans-N2O2 coordination environment around the metal center. The spectroscopic characteristics of HL1, HL2, 1, and 2 are consistent with their molecular structures. Both complexes were successfully employed as efficient catalysts in Kumada–Corriu C-C cross-coupling reactions of aryl bromides with phenylmagnesium bromide. The reactions provided biaryl products in good to excellent yields with a good substrate scope.

[Pd(4-R3Si-IPr)(allyl)Cl]/K2CO3/EtOH: A highly effective catalytic system for the Suzuki-Miyaura cross-coupling reaction

A series of R3Si-NHC-Pd complexes 1Pd-7Pd was successfully tested as a pre-catalyst for the Suzuki-Miyaura cross-coupling reaction of aryl chlorides and arylboronic acid derivatives to form a wide range of valuable biphenyl products. Use of the readily available weakly basic potassium carbonate as a base and the highly polar protic ethanol as the reaction solvent gave the target coupling products in good-to-excellent yields. The experimental data pointed to the crucial importance of the preliminary pre-catalyst activation step [i.e., the conversion of Pd(II) to Pd(0)], which is remarkably facilitated by the electron-donating trialkylsilyl groups on the NHC ligands of 1Pd–7Pd, thereby rendering them superior compared to the commercially available IPr-Pd complexes. Computational analysis revealed the mechanism of the Pd(II)→Pd(0) activation step, demonstrating the critical role of the reaction solvent and the base in the preference of our 1Pd–7Pd pre-catalysts, for which this step is both thermodynamically and kinetically more feasible.